4,4'-Dimethoxybenzhydrylamine → N-[(1S,2R,3S,4R)-4-(6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-2-chloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide

HRID 2382449Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2382449
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([NH:16][C:17](=[O:20])[CH2:18][CH3:19])[C@@H:13]([OH:21])[C@H:12]2[OH:22])=[C:4](Cl)[N:3]=1.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH:32]([NH2:41])[C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)=[CH:28][CH:27]=1>C1COCC1>[CH3:40][O:39][C:36]1[CH:35]=[CH:34][C:33]([CH:32]([NH:41][C:4]2[N:3]=[C:2]([Cl:1])[N:10]=[C:9]3[C:5]=2[N:6]=[CH:7][N:8]3[C@@H:11]2[CH2:15][C@H:14]([NH:16][C:17](=[O:20])[CH2:18][CH3:19])[C@@H:13]([OH:21])[C@H:12]2[OH:22])[C:29]2[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=2)=[CH:38][CH:37]=1

Komponenten

4

Edukt 2

HCID 3500424,4'-Dimethoxybenzhydrylamine2×HCID 86622629N-[(1S,2R,3S,4R)-4-(2,6-Dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide

Produkt 1

HCID 86643675N-[(1S,2R,3S,4R)-4-(6-{[Bis-(4-methoxy-phenyl)-methyl]-amino}-2-chloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of N-[(1S,2R,3S,4R)-4-(2,6-dichloro-purin-9-yl)-2,3-dihydroxy-cyclopentyl]-propionamide (Intermediate J7) (2.6 g, 7.22 mmol) in dry THF (26 ml) is added C,C-Bis-(4-methoxy-phenyl)-methylamine (Intermediate Y) (3.5 g, 14.44 mmol). The mixture is heated at 50° C. for 12 hours and then concentrated in vacuo. The residue is dissolved in chloroform and washed sequentially with 1.5N HCl, water and saturated aqueous brine solution. The organic phase is dried over anhydrous sodium sulphate and concentrated in vacuo. The crude product is purified by chromatography on silica (60-120 mesh) eluting with 2% methanol in chloroform to afford the title product. LC-MS (0.1% formic acid, acetonitrile): (MH+ 567)

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue is dissolved in chloroform
  3. washwashed sequentially with 1.5N HCl, water and saturated aqueous brine solution
  4. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by chromatography on silica (60-120 mesh)
  7. washeluting with 2% methanol in chloroform

Quellen und Nachweise

ORD-Eintrag
ord-b57fc483d74e473785b01265f3e37b3d
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258141B2

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